(2S,4R,5R)-6-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,4R,5R)-6-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 247115-06-6
• Molecular Formula: C₂₄H₂₃NO₆S
• Molecular Weight: 453.516

Synonyms:

Chemical Property of (2S,4R,5R)-6-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property:

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Technology Process of (2S,4R,5R)-6-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 3 articles about (2S,4R,5R)-6-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

benzhydryl 6-(Z)-(1-methoxycarbonylmethylene)penicillanate (167028-45-7) → (2S,4R,5R)-6-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (247115-06-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0960-894X(99)00325-X

Reference yield:

benzhydryl 6-oxopenicillinate (129792-01-4) → (2S,4R,5R)-6-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (247115-06-6)

Guidance literature:

Multi-step reaction with 2 steps

1: -78 °C

2: MCPBA / CH₂Cl₂

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0960-894X(99)00325-X

Reference yield:

6-aminopenicillanic acid diphenylmethyl ester (47547-28-4,78184-79-9) → (2S,4R,5R)-6-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (247115-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Me₂CHONO, TFA, 2.) Rh(OOct)4, propylene oxide

2: -78 °C

3: MCPBA / CH₂Cl₂

With rhodium (II) octanoate dimer; i-propyl nitrite; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; methyloxirane; In dichloromethane;

DOI:10.1016/S0960-894X(99)00325-X

upstream raw materials:

benzhydryl 6-(Z)-(1-methoxycarbonylmethylene)penicillanate

benzhydryl 6-oxopenicillinate

6-aminopenicillanic acid diphenylmethyl ester

Downstream raw materials:

(R)-2-{(R)-2-(Benzothiazol-2-yldisulfanyl)-3-[1-methoxycarbonyl-meth-(Z)-ylidene]-4-oxo-azetidin-1-yl}-3-methyl-but-3-enoic acid benzhydryl ester

(2S,3R,5R)-6-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3-methyl-3-[2-(1-methyl-1H-tetrazol-5-ylsulfanyl)-acetoxymethyl]-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,3R,5R)-3-(2-Chloro-acetoxymethyl)-6-[1-methoxycarbonyl-meth-(Z)-ylidene]-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,3R,5R)-3-Acetoxymethyl-6-[1-methoxycarbonyl-meth-(Z)-ylidene]-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

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